Midterm Flashcards by Jake Brooks

What is the structure for sodium borohydride?

Na+ BH4-

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What is the structure for Acetone?

CH3-(C=O)-CH3

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What is the structure for 9-Fluorenone?

Five carbon ring with a =O and two benzene rings attached on either side

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What is the structure for 9-Fluorenol?

Five carbon ring with a -OH and two benzene rings attached on either side

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What is the structure for Hexane?

C6H14

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What is the structure for Hydrogen Chloride?

HCl

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What is the structure for Methylene Chloride?

Cl-CH2-Cl

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What is the structure for Anhydrous Sodium Sulfate?

Na2SO4

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What is the structure for Chromium Trioxide?

CrO3

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What is the structure for Pyridinium chlorochromate?

6 membered ring with NH+ as one of the members, ClCrO3-

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What is the structure for 9-hydroxyfluorene?

Same as 9-Fluorenol, Two benzene rings attached to a five membered ring, with an OH attached to the five membered ring

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What is the structure for Dichloromethane?

CH2Cl2

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What is the structure for Methanol?

CH3OH

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What is the structure for Toluene?

Benzene-CH3

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What is the structure for Benzophenone?

Benzene-(C=O)-Benzene

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What is the structure for Bromobenzene?

Benzene-Br

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What is the structure for Triphenylmethanol?

HO-C-(Ph)3

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What is the structure for (di)-Ethyl Ether?

CH3CH2OCH2CH3

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What is the structure for Hydrochloric Acid?

HCl

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What is the structure for Biphenyl?

Ph-Ph

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What is the structure for Isopropyl Alcohol?

Three carbon long chain with -OH on the middle carbon

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What is the structure for Benzil?

Ph-(C=O)-(C=O)-Ph

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What is the structure for 1,3-diphenylacetone?

Ph-C-(C=O)-C-Ph

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What is the structure for Tetraphenylcyclopentadienone?

Four benzene rings attached to with a bond to a five membered double bonded carbon ring

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air condenser

straight tube

casserole

clay cup on a stick

claisen adapter

tube that separates into two, U shaped

crucible tongs

go outward, for holding hot beakers and such

drying tube

tube that takes a hard right

Hickman still head

the tube that looks kinda squished down, tiny tube going into larger tube

jacked water condenser

two side ports, shell around tube

stirring rod with rubber policeman

glass rod, pointy rubber tip

sublimation adapter

short piece of glass with side port and slanted bottom

test tube clamp

holder part is little curved rectangles

thistle tube

looks like a vase on a stick

vacuum filter flask

large erlenmeyer with side port

Where are the safety showers? (2)

In both corners on the hallway side

Where are the fire blankets? (2)

In both corners on the hallway side, in the left corner the blanket is to the right of the cart

Where is the eyewash station? (1)

On the second station from the left

Where are the fire extinguishers? (3)

To the left of each hood when facing into the lab, and in the right corner by the hallway

Balanced reaction for reduction experiment

(4) 9-fluorenone + Sodium Borohydride -> (4) 9-fluorenol

Reaction with HCl in reduction experiment

produce hydrogen gas by reacting with excess NaBH4 and water to produce NaCl, H3BO3, and H2

Isolation of oxidation product

cold vacuum filtration with Ch2Cl2 rinses, then dried to remove CH2Cl2

TLC, effect of polarity of spot on Rf

more polar, lower Rf

Balanced reaction for grignard experiment (both)

Bromobenzene + Mg -> Phenylmagnesium Bromide + Benzophenone -> triphenylmethanol

Reaction with HCl in grignard experiment

react with excess Mg to produce hydrogen gas

Balanced reaction for aldol experiment

benzil + 1,3-diphenylacetone -> tetraphenylcyclopentadienone

Mechanism of self-condensation, acetophenone

OH removes alpha hydrogen -> negative C attaches to carbonyl C, making that O negative -> reacts with water produced in step one to turn negative O into OH, produces OH -> electrons are moved from double bond up to O and OH removes another alpha hydrogen, producing water -> double bonds are made on the original O and from the carbon that kept getting hydrogens removed to carbonyl carbon, OH is leaving group

What is the ratio between NaBH4 and its reactants?

1:4

Define oxidation and reduction

Oxidation: Increase O or decrease H, Reduction: Decrease O or increase H

Describe the half-cell method for balancing redox reactions

balance non H and O atoms -> balance O by adding H2O -> balance H by adding H+ -> balance charge by adding e- -> multiply both half-cells to match

What reaction is avoided by keeping glassware dry in the Grignard experiment?

RMgX + H2O -> RH + Mg + OH

What is the reactivity of halogens in grignard reagents?

I>Br>Cl

What side reaction does RMgX make during its creation? How can this be avoided?

RMgX + RX -> RR + MgX2 | Add bromobenzene slowly

What is the reaction grignard reagents make with oxygen?

RMgX + O2 -> ROOH + ROH + HOMgX

Reaction rates double with each ----------- increase

10*C

What are some problems with changing solvents? (for grignard, but could apply broadly)

Reactants not soluble, side reactions at higher BP, difficult to remove solvent

What is the reaction that occurs with the triphenylmethanol to produce a red color?

Triphenylmethanol + H2SO4 -> Ph3COH2+ -> Ph3C+ and H2O

What are the limitations of an aldol reaction?

Reactants with only one alpha hydrogen cannot dehydrate, reactants without any alpha hydrogens cannot undergo reaction

Name and describe naturally occuring aldol products

Chalcones, Ketone where one side is benzene and the other is C=C-Ph

Describe the orientation of tetraphenylcyclopentadienone

Not planar, due to steric crowding

When are dehydrated intermediates favored in aldol reactions?

lower temp, lower base concentration

In the reduction experiment, what is the side reaction with NaBH4 and the product?

NaBH4 + ROH -> NaB(OR)4 + H2

What are the two layers in the reduction experiment?

top is stuff like H2BO3, NaCl, and HCl | bottom is 9-fluorenol, 9-fluorenone

Describe glassware setup for reduction experiment

conical vial + claisen adaptor + water jacketed condenser (on non-vial side)

Describe the glassware setup for the grignard experiment

Conical vial + claisen adaptor + syringe (vial side) and water-jacketed condenser with drying tube (non-vial side)

How can you help initiate a grignard experiment?

crushing/scratching Mg, adding I2, adding 1,2-dibromoethane, adding PhMgBr, ultrasound, heating

Describe the drying agent for the grignard experiment and the indication of its hydration

drierite, CaSO4, blue to pink

Describe the two layers formed during grignard workup

Top is Ph3COH and biphenyl, bottom is HCl, MgCl2

What is another name for trituration

grinding

How is the product isolated in the grignard experiment

add hexane, vacuum filtration